1,2-Dichloroethane → Cinnamoylbenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 44 mg (0.11 mmol) a D-glucopyranosylnitromethane tetra-acetate (alpha anomer) and 24 μL (0.22 mmol) phenyl isocyanate in 0.80 mL 1,2-dichloroethane containing 30 mg (0.016 mmol) Rink Amide Resin bound compound 1, 2 mL (0.016 mmol) triethylamine was added under argon. The mixture was refluxed and shaken at 78° C. for 15 hours. It was allowed to cool down to room temperature. The resin bound compound 2 was collected in a 3 mL filtering column and was washed with N,N-dimethylformamide (3×2 mL), methylene chloride (3×2 mL) and dried under vacuum. The dried Resin bound compound 2 was treated with 2 mL 20% trifluoroacetic acid in methylenechloride for 20 minutes. The solid was filtered off and washed 3 times with 1.5 mL methylene chloride. The combined washings were concentrated and dried under vacuum to give 12 mg product 3 of ca. 95% purity. The spectral data consisted of: Electrospray MS m/z 884 (M+ +1). ##STR60##

Provenance & Evidence